A new cytotoxic and tubulin-interactive milnamide derivative from a marine sponge Cymbastela sp.

被引:35
作者
Chevallier, C
Richardson, AD
Edler, MC
Hamel, E
Harper, MK
Ireland, CM [1 ]
机构
[1] Univ Utah, Dept Med Chem, Salt Lake City, UT 84112 USA
[2] NCI, Div Canc Treatment & Diagnosis, Dev Therapeut Program, Screening Technol Branch,NIH, Ft Detrick, MD 21702 USA
关键词
D O I
10.1021/ol035476c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The crude methanol extract of a marine sponge Cymbastela sp. collected in Papua New Guinea was selected for chemical investigation due to its significant cytotoxicity. Fractionation of the extract led to the isolation of jaspamide (1), hemiasterlin (2), milnamide A (3), and a new metabolite, milnamide D (4). The structure was solved by interpretation of NMR and mass spectra data. The cytotoxic and antitubulin activities of milinamide D (4) were evaluated.
引用
收藏
页码:3737 / 3739
页数:3
相关论文
共 10 条
  • [1] Anderson HJ, 1997, CANCER CHEMOTH PHARM, V39, P223
  • [2] Interactions of the sponge-derived antimitotic tripeptide hemiasterlin with tubulin: Comparison with dolastatin 10 and cryptophycin 1
    Bai, RL
    Durso, NA
    Sackett, DL
    Hamel, E
    [J]. BIOCHEMISTRY, 1999, 38 (43) : 14302 - 14310
  • [3] CARMICHAEL J, 1987, CANCER RES, V47, P936
  • [4] CYTOTOXIC PEPTIDES FROM THE MARINE SPONGE CYMBASTELA SP
    COLEMAN, JE
    DESILVA, ED
    KONG, FM
    ANDERSEN, RJ
    ALLEN, TM
    [J]. TETRAHEDRON, 1995, 51 (39) : 10653 - 10662
  • [5] MILNAMIDE-A, AN UNUSUAL CYTOTOXIC TRIPEPTIDE FROM THE MARINE SPONGE AULETTA-CF-CONSTRICTA
    CREWS, P
    FARIAS, JJ
    EMRICH, R
    KEIFER, PA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) : 2932 - 2934
  • [6] Cytotoxic and tubulin-interactive hemiasterlins from Auletta sp and Siphonochalina spp. sponges
    Gamble, WR
    Durso, NA
    Fuller, RW
    Westergaard, CK
    Johnson, TR
    Sackett, DL
    Hamel, E
    Cardellina, JH
    Boyd, MR
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (08) : 1611 - 1615
  • [7] Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin
    Hamel, E
    [J]. CELL BIOCHEMISTRY AND BIOPHYSICS, 2003, 38 (01) : 1 - 21
  • [8] SEPARATION OF ACTIVE TUBULIN AND MICROTUBULE-ASSOCIATED PROTEINS BY ULTRACENTRIFUGATION AND ISOLATION OF A COMPONENT CAUSING THE FORMATION OF MICROTUBULE BUNDLES
    HAMEL, E
    LIN, CM
    [J]. BIOCHEMISTRY, 1984, 23 (18) : 4173 - 4184
  • [9] HEMIASTERLIN AND GEODIAMOLIDE-TA - 2 NEW CYTOTOXIC PEPTIDES FROM THE MARINE SPONGE HEMIASTERELLA-MINOR (KIRKPATRICK)
    TALPIR, R
    BENAYAHU, Y
    KASHMAN, Y
    PANNELL, L
    SCHLEYER, M
    [J]. TETRAHEDRON LETTERS, 1994, 35 (25) : 4453 - 4456
  • [10] JASPAMIDE, A MODIFIED PEPTIDE FROM A JASPIS SPONGE, WITH INSECTICIDAL AND ANTIFUNGAL ACTIVITY
    ZABRISKIE, TM
    KLOCKE, JA
    IRELAND, CM
    MARCUS, AH
    MOLINSKI, TF
    FAULKNER, DJ
    XU, CF
    CLARDY, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) : 3123 - 3124